JP6804085B2 - Tyrosinase activity inhibitors, pharmaceuticals, cosmetics and food anti-browning agents - Google Patents
Tyrosinase activity inhibitors, pharmaceuticals, cosmetics and food anti-browning agents Download PDFInfo
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- 102000003425 Tyrosinase Human genes 0.000 title claims description 41
- 108060008724 Tyrosinase Proteins 0.000 title claims description 41
- 230000000694 effects Effects 0.000 title claims description 38
- 239000003112 inhibitor Substances 0.000 title claims description 33
- 239000002537 cosmetic Substances 0.000 title claims description 16
- 235000013305 food Nutrition 0.000 title claims description 13
- 239000003814 drug Substances 0.000 title description 5
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- 241000972773 Aulopiformes Species 0.000 claims description 6
- 235000019515 salmon Nutrition 0.000 claims description 6
- 102000035195 Peptidases Human genes 0.000 claims description 5
- 108091005804 Peptidases Proteins 0.000 claims description 5
- 210000002184 nasal cartilage Anatomy 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
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- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 8
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- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 5
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- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
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- 241000238557 Decapoda Species 0.000 description 2
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- 241000251468 Actinopterygii Species 0.000 description 1
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- 240000000599 Lentinula edodes Species 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
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- 101710147108 Tyrosinase inhibitor Proteins 0.000 description 1
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- 238000003287 bathing Methods 0.000 description 1
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- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
Description
本発明は、チロシナーゼ活性阻害剤及びこのチロシナーゼ活性阻害剤を用いた医薬品、化粧品、食品褐変防止剤に関するものである。 The present invention relates to a tyrosinase activity inhibitor and a pharmaceutical product, cosmetics, and food browning inhibitor using the tyrosinase activity inhibitor.
メラニンは、動物組織内にある色素であり、紫外線から皮膚や組織を保護することがその大きな役割である。しかしながら、皮膚での過剰なメラニンの産生はシミ、ソバカス、斑点などの原因になっている。そしてメラニン色素の生成に関わる酸化酵素の一つとしてチロシナーゼが知られている。 Melanin is a pigment found in animal tissues, and its major role is to protect skin and tissues from ultraviolet rays. However, excessive production of melanin in the skin causes spots, freckles, and spots. Tyrosinase is known as one of the oxidases involved in the production of melanin pigment.
チロシナーゼの活性を阻害することでメラニンの生成を抑制することができれば、美白効果につながることから、チロシナーゼ活性阻害剤は化粧品素材として広く利用されている（特許文献１及び特許文献２参照）。特許文献１及び特許文献２等に開示されているチロシナーゼ活性阻害剤やメラニン生成抑制剤は、いずれも効果、安全性、安定性、コスト等の観点において必ずしも十分であるとはいえなかった。
If the production of melanin can be suppressed by inhibiting the activity of tyrosinase, it leads to a whitening effect. Therefore, the tyrosinase activity inhibitor is widely used as a cosmetic material (see
本発明は、優れたチロシナーゼ活性阻害効果を有するとともに、安心感の昂揚や積極的使用に貢献できるチロシナーゼ活性阻害剤及びこのチロシナーゼ活性阻害剤を用いた医薬品、化粧品、食品褐変防止剤を提供することを目的とする。 The present invention provides a tyrosinase activity inhibitor which has an excellent tyrosinase activity inhibitory effect and can contribute to a feeling of security and active use, and a pharmaceutical product, cosmetics, and food browning inhibitor using this tyrosinase activity inhibitor. With the goal.
本発明者らは、上記課題を達成するために種々検討した結果、サケ鼻軟骨プロテオグリカンをタンパク質分解酵素アクチナーゼＥで消化して得られた低分子化プロテオグリカンに優れたチロシナーゼ活性阻害効果があることを見出し、本発明を完成させた。 As a result of various studies to achieve the above problems, the present inventors have found that the low molecular weight proteoglycan obtained by digesting salmon nasal cartilage proteoglycan with the proteolytic enzyme actinase E has an excellent tyrosinase activity inhibitory effect. The heading has completed the present invention.
すなわち、本発明は下記（１）〜（５）まで掲げる態様を含むものである。
（１）サケ鼻軟骨プロテオグリカンをタンパク質分解酵素アクチナーゼＥで消化して得られた低分子化プロテオグリカンを有効成分とするチロシナーゼ活性阻害剤であることを要旨とする。
（２）前記（１）に記載の低分子化プロテオグリカンを０．０００３３重量％以上含むチロシナーゼ活性阻害剤であることを要旨とする。
（３）前記（１）に記載の低分子化プロテオグリカンを含む皮膚外用剤であることを要旨とする。
（４）前記（１）に記載の低分子化プロテオグリカンを含む美白化粧料であることを要旨とする。
（５）前記（１）に記載の低分子化プロテオグリカンを含む食品褐変防止剤であることを要旨とする。
That is, the present invention includes the aspects listed in (1) to (5) below.
(1) The gist is that it is a tyrosinase activity inhibitor containing low molecular weight proteoglycan obtained by digesting salmon nasal cartilage proteoglycan with the proteolytic enzyme actinase E as an active ingredient.
(2) The gist is that it is a tyrosinase activity inhibitor containing 0.00033% by weight or more of the low molecular weight proteoglycan described in (1) above.
(3) The gist is that it is a skin external preparation containing the low molecular weight proteoglycan described in (1) above.
(4) The gist is that it is a whitening cosmetic containing the low molecular weight proteoglycan described in (1) above.
(5) The gist is that it is a food browning inhibitor containing the low molecular weight proteoglycan described in (1) above.
本発明によれば、優れたチロシナーゼ活性阻害効果を有していること、また、従来から非常に強力な活性を有することがよく知られているコウジ酸と比較しても、より強いチロシナーゼ活性阻害効果を示すことが明らかとなり、且つ天然物を原料としていることから、安心感の昂揚や積極的使用に貢献できるチロシナーゼ活性阻害剤及びこのチロシナーゼ活性阻害剤を用いた医薬品、化粧品、食品褐変防止剤が提供できる。 According to the present invention, it has an excellent inhibitory effect on tyrosinase activity, and even stronger inhibition of tyrosinase activity than kojic acid, which is well known to have a very strong activity in the past. A tyrosinase activity inhibitor that has been shown to be effective and is made from natural products, which can contribute to a sense of security and active use, and pharmaceuticals, cosmetics, and food browning inhibitors using this tyrosinase activity inhibitor. Can be provided.
以下、実施の形態をより具体的に説明するが、本発明の技術的思想を具体化するための方法を例示するものであって、本発明の技術的思想は、下記のものに特定するものではない。本発明の技術的思想は、特許請求の範囲に記載された請求項が規定する技術的範囲内において、種々の変更を加えることができる。 Hereinafter, embodiments will be described in more detail, but the method for embodying the technical idea of the present invention is exemplified, and the technical idea of the present invention is specified as follows. is not. The technical idea of the present invention may be modified in various ways within the technical scope specified by the claims stated in the claims.
本発明の実施の形態に係る原料プロテオグリカンは、魚類に存在するグリコサミノグリカンとタンパク質の共有結合物からなる分子量数十万から数百万の高分子化合物である。 The raw material proteoglycan according to the embodiment of the present invention is a polymer compound having a molecular weight of several hundred thousand to several million, which is composed of a covalent bond of glycosaminoglycan and a protein existing in fish.
本発明の実施の形態に係る低分子化プロテオグリカンは、サケ鼻軟骨由来原料プロテオグリカンをタンパク質分解酵素であるアクチナーゼＥにより消化することで製造することができる。 The low molecular weight proteoglycan according to the embodiment of the present invention can be produced by digesting salmon nasal cartilage-derived raw material proteoglycan with actinase E, which is a proteolytic enzyme.
前記原料プロテオグリカンは、青森県などの郷土料理としてよく知られている「氷頭なます」をヒントに工業原料として実用化されたもので、食経験のあるサケ鼻軟骨から酢酸を用いて抽出されており、安心感の昂揚や積極的使用に貢献できるものである。 The raw material proteoglycan was put into practical use as an industrial raw material with the hint of "Hito Namasu", which is well known as a local dish in Aomori prefecture, and is extracted from salmon nasal cartilage with eating experience using acetic acid. It can contribute to raising the sense of security and active use.
本発明の実施の形態に係る低分子化プロテオグリカンには、優れたチロシナーゼ活性阻害効果があり、医薬品、化粧品あるいは食品褐変防止剤に利用することができる。 The low-molecular-weight proteoglycan according to the embodiment of the present invention has an excellent inhibitory effect on tyrosinase activity and can be used in pharmaceuticals, cosmetics or food browning inhibitors.
以下に実施例を示して本発明の実施の形態を具体的に説明するが、これは単に例示の目的で述べるものであり、本発明はこれらの実施例に限定されるものではない。 Hereinafter, embodiments of the present invention will be specifically described with reference to Examples, but the present invention is merely described for the purpose of illustration, and the present invention is not limited to these Examples.
（低分子化プロテオグリカンの製造）
原料プロテオグリカン（市販の鮭由来プロテオグリカン：角弘プロテオグリカン研究所社製）を、タンパク質分解酵素アクチナーゼＥ（科研製薬製）を用いて消化し、得られた分解生成物をセファアクリルＳ−５００ＨＲゲルろ過クロマトグラフィー（Ｖ０＝２２０ｍＬ、Ｖｔ＝５８９ｍＬ）により精製し、溶出位置３５０ｍＬから５５０ｍＬまでの画分を集め（４１０ｋＤａデキストランの溶出位置は４０７ｍＬ）、低分子化プロテオグリカンとした。この低分子化プロテオグリカンを試料としてチロシナーゼ活性阻害試験を行った。
(Manufacturing of low molecular weight proteoglycan)
The raw material proteoglycan (commercially available salmon-derived proteoglycan: manufactured by Kakuhiro Proteoglycan Research Institute) was digested using the proteolytic enzyme actinase E (manufactured by Kaken Pharmaceutical Co., Ltd.), and the obtained decomposition product was subjected to Sephaacrylic S-500HR gel filtration chromatography. Purification was performed by (V 0 = 220 mL, V t = 589 mL), and fractions from the elution positions of 350 mL to 550 mL were collected (the elution position of 410 kDa dextran was 407 mL) to obtain low molecular weight proteoglycans. A tyrosinase activity inhibition test was conducted using this low molecular weight proteoglycan as a sample.
（低分子化プロテオグリカンを用いたチロシナーゼ活性阻害試験）
マッシュルーム由来チロシナーゼ（シグマ社製）を０．１Ｍリン酸緩衝液（ｐＨ６．８）に溶解して酵素溶液（４０Ｕ／ｍＬ）とした。基質はＬ−ＤＯＰＡ（３，４−Ｄｉｈｙｄｒｏｘｙ−Ｌ−ｐｈｅｎｙｌａｌａｎｉｎｅ，シグマ社製）を用い、０．１Ｍリン酸緩衝液（ｐＨ６．８）に溶解して２ｍＭの基質溶液とした。各濃度の低分子化プロテオグリカン溶液を調製し、陽性対照にはコウジ酸（東京化成製）を用いた。酵素反応は、９６穴マイクロプレートにて行った。マイクロプレートの各ウェルに酵素溶液５０μＬと阻害剤５０μＬを加え、充分混合攪拌した。室温で２分間プレインキュベートした後、基質であるＬ−ＤＯＰＡ溶液を５０μＬ添加し、３７℃で１０分間インキュベートした。その後、マイクロプレートリーダー（ＴｒｉＳｔａｒ ＬＢ９４１、ベルトールドジャパン社製）を用いて、波長４５０ｎｍにおける吸光度を測定した。チロシナーゼ活性阻害剤を用いない区分（チロシナーゼの活性を阻害していないもの）の吸光度をＡ、各阻害剤を添加した区分（チロシナーゼの活性を阻害したもの）の吸光度をＢとし、チロシナーゼ阻害率を 阻害率（％）＝｛（Ａ−Ｂ）／Ａ｝×１００ として計算した。
(Tyrosinase activity inhibition test using low molecular weight proteoglycan)
Mushroom-derived tyrosinase (manufactured by Sigma) was dissolved in 0.1 M phosphate buffer (pH 6.8) to prepare an enzyme solution (40 U / mL). As a substrate, L-DOPA (3,4-Dihydroxy-L-phenylalanine, manufactured by Sigma) was used and dissolved in 0.1 M phosphate buffer (pH 6.8) to prepare a 2 mM substrate solution. A low-molecular-weight proteoglycan solution of each concentration was prepared, and kojic acid (manufactured by Tokyo Kasei) was used as a positive control. The enzymatic reaction was carried out on a 96-well microplate. 50 μL of the enzyme solution and 50 μL of the inhibitor were added to each well of the microplate, and the mixture was thoroughly mixed and stirred. After pre-incubating at room temperature for 2 minutes, 50 μL of the substrate L-DOPA solution was added and incubated at 37 ° C. for 10 minutes. Then, using a microplate reader (TriStar LB941, manufactured by Berthold Japan Co., Ltd.), the absorbance at a wavelength of 450 nm was measured. The absorbance of the category without the tyrosinase activity inhibitor (the one that does not inhibit the activity of tyrosinase) is A, the absorbance of the category with each inhibitor added (the one that inhibits the activity of tyrosinase) is B, and the tyrosinase inhibition rate is defined as B. Inhibition rate (%) = {(AB) / A} × 100.
低分子化プロテオグリカン及び陽性対照であるコウジ酸を用いてマッシュルーム由来チロシナーゼ活性に対する阻害効果を調べた結果を図１に示す。低分子化プロテオグリカンは陽性対照であるコウジ酸よりも強い阻害効果を示した。低分子化プロテオグリカンは濃度３．３、９．９、３３、９９、３３０、９９０μｇ／ｍＬにおいて、マッシュルーム由来チロシナーゼ活性をそれぞれ１８．０、２５．６、５３．４、７８．８、８２．９、８４．９％阻害した。一方、陽性対照であるコウジ酸は濃度２０、４０、６０、８０、１００μｇ／ｍＬにおいて、マッシュルーム由来チロシナーゼ活性をそれぞれ３６.１、５３．３、６５．１、６８．５、７０．４％阻害した。これらの結果から、マッシュルーム由来チロシナーゼ活性に対する低分子化プロテオグリカン及びコウジ酸の５０％阻害濃度ＩＣ５０は、それぞれ２８．５、３５．３μｇ／ｍＬと計算され、低分子化プロテオグリカンには、コウジ酸よりも１．２４倍の強いチロシナーゼ活性阻害効果があることが分かった。なお、原料プロテオグリカンには顕著なチロシナーゼ活性阻害効果は見られなかった。 The results of examining the inhibitory effect on mushroom-derived tyrosinase activity using low-molecular-weight proteoglycan and kojic acid, which is a positive control, are shown in FIG. Low-molecular-weight proteoglycans showed a stronger inhibitory effect than the positive control kojic acid. Low-molecular-weight proteoglycans exhibited mushroom-derived tyrosinase activity at concentrations of 3.3, 9.9, 33, 99, 330, and 990 μg / mL, respectively, at 18.0, 25.6, 53.4, 78.8, and 82.9, respectively. , 84.9% inhibition. On the other hand, kojic acid, which is a positive control, inhibits mushroom-derived tyrosinase activity by 36.1, 53.3, 65.1, 68.5, and 70.4% at concentrations of 20, 40, 60, 80, and 100 μg / mL, respectively. did. From these results, the 50% inhibitory concentrations of IC50 of low molecular weight proteoglycan and codic acid for mushroom-derived tyrosinase activity were calculated to be 28.5 and 35.3 μg / mL, respectively, and the low molecular weight proteoglycan was more suitable than codic acid. It was found that it has a 1.24-fold stronger inhibitory effect on tyrosinase activity. The raw material proteoglycan did not show a remarkable inhibitory effect on tyrosinase activity.
本発明のチロシナーゼ活性阻害剤は、従来のチロシナーゼ活性阻害剤と同様に、医薬品、化粧品及び食品褐変防止剤の有効成分として利用可能である。この場合、チロシナーゼ阻害剤の添加量は、特に限定されるものではなく、皮膚外用剤や化粧料、食品褐変防止剤の種類によって異なるが、目的にあわせて適宜配合すればよい。 The tyrosinase activity inhibitor of the present invention can be used as an active ingredient of pharmaceuticals, cosmetics and food browning inhibitor, like the conventional tyrosinase activity inhibitor. In this case, the amount of the tyrosinase inhibitor added is not particularly limited, and varies depending on the type of external preparation for skin, cosmetics, and food browning inhibitor, but may be appropriately blended according to the purpose.
本発明のチロシナーゼ活性阻害剤を皮膚外用剤として利用する場合、その形態としては、軟膏剤、クリーム剤、乳剤、ゲル剤、ローション剤、トリートメント剤、貼付剤などが挙げられる。 When the tyrosinase activity inhibitor of the present invention is used as an external preparation for skin, its form includes an ointment, a cream, an emulsion, a gel, a lotion, a treatment agent, a patch and the like.
また、本発明のチロシナーゼ活性阻害剤を化粧料として利用する場合、その形態としては、クリーム、乳液、ローション、化粧水、ジェル、美容液、パックなどの基礎化粧品、また、日焼け止めクリーム、日焼け止めローション、日焼け止めリップクリームなどの日焼け止め化粧料、また、メイクアップベースクリーム、パウダーファンデーション、リキッドファンデーション、口紅などのメイクアップ化粧料、さらには、ハンドクリーム、レッグクリーム、ボディローション、浴用剤などのボディ用化粧料などが挙げられる。 When the tyrosinase activity inhibitor of the present invention is used as a cosmetic, its form includes basic cosmetics such as creams, milky lotions, lotions, lotions, gels, beauty liquids, and packs, as well as sunscreen creams and sunscreens. Sunscreen cosmetics such as lotions and sunscreen lip creams, makeup cosmetics such as makeup base creams, powder foundations, liquid foundations and lipsticks, as well as hand creams, leg creams, body lotions and bathing agents. Examples include body cosmetics.
さらに、本発明のチロシナーゼ活性阻害剤を食品褐変防止剤として利用する場合、その対象となる食品としては、各種フルーツ、椎茸、マッシュルームなどのきのこ類、カニやエビなどの海産物などが挙げられる。その使用方法としては、本発明の阻害剤を適当な媒体で希釈し、この溶液を対象物に噴霧、浸漬させることで食品表面の褐変を防止することができる。 Furthermore, when the tyrosinase activity inhibitor of the present invention is used as a food browning inhibitor, the target foods include various fruits, mushrooms such as shiitake mushrooms and mushrooms, and marine products such as crabs and shrimp. As a method of its use, the inhibitor of the present invention is diluted with an appropriate medium, and this solution is sprayed and immersed in an object to prevent browning of the food surface.
本発明の低分子化プロテオグリカンは、優れたチロシナーゼ阻害活性を有し、しかも、青森県などの郷土料理としてよく知られている「氷頭なます」をヒントに工業原料として実用化されたプロテオグリカンから酵素分解により得られる物質であるため、安心感の昂揚や積極的使用に貢献できるものである。従って、低分子化プロテオグリカンを有効成分とするチロシナーゼ活性阻害剤は、医薬品、化粧品あるいは食品褐変防止剤の分野で広く利用することが可能である。
The low-molecular-weight proteoglycan of the present invention has excellent tyrosinase inhibitory activity, and is derived from proteoglycan that has been put into practical use as an industrial raw material with the hint of "Hito-Namasu", which is well known as a local dish in Aomori Prefecture. Since it is a substance obtained by enzymatic decomposition, it can contribute to raising a sense of security and active use. Therefore, a tyrosinase activity inhibitor containing a low molecular weight proteoglycan as an active ingredient can be widely used in the fields of pharmaceuticals, cosmetics or food browning preventive agents.
Claims (5)
The food browning inhibitor containing the low molecular weight proteoglycan according to claim 1.
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